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N-bromobutanimide → 5-[5-bromo-4-(2-bromophenyl)-4H-1,2,4-triazol-3-yl]-2-phenylpyridine

HRID 6922
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 6922
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[N:11][N:10]=[C:9]1[C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:17][CH:18]=1.C1C(=O)N([Br:32])C(=O)C1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)(Cl)Cl.C(O)(=O)C>[Br:32][C:12]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[C:9]([C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:17][CH:18]=2)=[N:10][N:11]=1
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Komponenten

6

Edukt 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 220192605-[4-(2-Bromophenyl)-4h-1,2,4-triazol-3-yl]-2-phenylpyridine

Produkt 1

HCID 220192295-[5-bromo-4-(2-bromophenyl)-4H-1,2,4-triazol-3-yl]-2-phenylpyridineAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic Acid
Lösungsmittel
HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

5-[4-(2-Bromophenyl)-4H-1,2,4-triazol-3-yl]-2-phenylpyridine prepared in the Production Example 2 was dissolved in a mixture solvent of carbon tetrachloride (100 ml) and acetic acid (100 ml), followed by addition of n-bromosuccinimide (5.90 g), and refluxed under heating for 3 hours. After the reaction solution was cooled to ambient temperature, the solution was concentrated-under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the resulting residue, and extracted with chloroform. Subsequently, the organic layer was dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1), to afford the entitled compound as yellow solid (6.96 g, 69%). The physico-chemical values are as follows.

Aufarbeitung

  1. temperaturerefluxed
  2. temperatureunder heating for 3 hours
  3. extractionextracted with chloroform
  4. dry with materialSubsequently, the organic layer was dried over anhydrous magnesium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-ffac4d3930b0426da52d569c2e6fa4ff
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07084164B2

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